Formaldehyde → HCID 42602277, compound

Participants

Reaction Steps

To a solution of 2-(1-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-1,3-dihydroisobenzofuran-1-yl)ethanamine (40 mg, 95.4 μmol) in acetonitrile (2 mL) at 0° C. was added formalin (0.250 mL) and then sodium cyanoborohydride (30 mg, 0.48 mmol). The ice bath was removed and stirring continued for 1 h, occasionally treating with a drop of acetic acid to keep the pH slightly less than 7. The reaction was concentrated, diluted with ether, washed with 1 M sodium hydroxide, then brine, dried over sodium sulfate, and concentrated. Column chromatography (4% MeOH/DCM) gave 28.5 mg (67%) as a colorless oil. 1H-NMR (CDCl3, 300 MHz) δ 7.75 (s, 1H), 7.64 (s, 2H), 7.30 (m, 2H), 7.15-7.25 (m, 2H), 5.11 (qAB, JAB=120.5 Hz, 2H), 4.62 (qAB, JAB=13.4 Hz, 2H), 3.67 (qAB, JAB=10.1 Hz, 2H), 2.41 (ddd, J=11.3, 11.3, 5.5 Hz, 1H), 2.20 (s, 6H), 2.19 (m, 1H), 1.98-2.14 (m, 2H); 13C-NMR (CDCl3, 126 MHz) δ 141.3, 141.2, 139.9, 131.7 (q, J=33.6 Hz), 128.2, 127.6, 126.1, 123.4 (q, J=273 Hz), 121.6, 121.4, 121.1, 89.5, 76.8, 72.9, 72.0, 54.3, 45.4, 34.4. Mass spec.: 448.22 (MH)+. Accurate mass spec.: m/z 448.1711 [MH]+, Δ=0.6 ppm.

Provenance & Evidence